Tributyltin compounds

Poller (498, 544) prepared a number of tributyl- and triphenyl-stan-nyl esters of sucrose hydrogenphthalate and succinate, and found that, as potential antifoulants, these were at least three times as effective against the marine alga, Enteromorpka, as bis(tributyltin) oxide, even though they contain almost one third the tin (see Table VIII). A new antifouling paint that also contains tributyltin compounds has recently been developed in Norway (545). 

Butyltin compounds, in contrast, are produced only anthropogenically. Besides the applications covered in this CICAD, there exist other applications of butyltin compounds that may represent a significant source of these substances in the environment. In particular, the use of tributyltin compounds in antifouling coatings represents a significant source of these substances in the marine and freshwater environments. Hence, many of the measured concentrations reported will relate predominantly to this use. 

IPOS (1990) Tributyltin compounds. Geneva, World Health Organization, International Programme on Chemical Safety (Environmental Health Criteria 116). 

Snoeij NJ, Penniks AH, Seinen W (1988) Dibutyltin and tributyltin compounds induce thymus atrophy in rats due to seiective action on thymic iymphobiasts. InternationalJournalof Immunopharmacology, 10 891-899. 

Tributyltin compounds used as antifouling agents on boats have had serious toxic effects upon many mollusks, including populations of oysters and dog whelks. Females of the latter species developed a condition known as imposex, which rendered them infertile and caused local extinction of the population in shallow coastal waters. Imposex provides the basis for a valuable biomarker assay. 

Environmental Health Criteria 116 (1990). Tributyltin compounds. Geneva WHO. 

Stang PM, RF Lee, PF Seligman (1992) Evidence for rapid, nonbiological degradation of tributyltin compounds in autoclaved and heat-treated fine-grained sediments. Environ Sci Technol 26 1382-1387. 

Laughlin, R. and O. Linden. 1982. Sublethal responses of the tadpoles of the European frog Rana temporaria to two tributyltin compounds. Bull. Environ. Contam. Toxicol. 28 494-499. 

Laughlin, R., K. Nordlund, and O. Linden. 1984. Long-term effects of tributyltin compounds on the Baltic amphipod, Gammarus oceanicus. Mar. Environ. Res. 12 243-271. 

Smith, B.S. 1981b. Tributyltin compounds induce male characteristics on female mud snails Nassarius obsoletus = Ilyanassa obsoleta. Jour. Appl. Toxicol. 1 141-144. 

Muller [76] has described a gas chromatographic method for the determination of tributyltin compounds in sediments. The tributyltin compounds are first converted to tributylmethyltin by reaction with ethyl magnesium bromide, and then analysed using capillary gas chromatography with flame photometric detection and gas chromatography-mass spectrometry. Tributyltin was found in samples of sediment and these results demonstrated that the technique has detection limits of less than 0.5pg L 1. 

An analogous mechanism was proposed for the conversion of the triflate 416 to the vinyl-, allyl- and allenyl-A2-cephems 448 in yields of 47-71% by the respective tributyltin compounds in the presence of cuprous chloride (Scheme 6.91) [176]. Accordingly, the cyclic allene 417 should be liberated from 416 in the first step. Then, the organocopper species would transfer a hydrocarbon group to the central allene carbon atom of 417, leading to an allyl anion derivative, which is protonated during the workup. These reactions of 416 and 443 indicate that the cyclic allenes 417 and 444 behave toward nucleophiles as 1,2-cyclohexadiene (6) (Schemes 6.11— 13) and its non-polar derivatives such as 215 (Scheme 6.51), 221 (Scheme 6.52), 311 (Scheme 6.67) and 333 (Schemes 6.71 and 6.73), that is, they interact with nucleophiles at the central carbon atom of the allene system exclusively. 

Gadd, G.M. Microbial interactions with tributyltin compounds detoxification, accumulation, and environmental fate. Sci. Total Environ. 2000, 258, 119-227. 

Tributyltin Workers exposed to the vapor or fume of tributyltin compounds developed sore throat and cough several hours after exposure. When a worker was splashed in the face with a tributyltin compound, lacrimation and severe conjunctivitis appeared within minutes, despite immediate lavage, and persisted for 4 days. At the end of 7 days, the eyes appeared normal. Chemical burns may result after only brief contact with the skin. Pain is usually moderate, and itching is the chief symptom. Healing is usually complete within 7-10 days. ... 

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